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Molecules
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Photocatalytic Strategies in Organic Synthesis
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Photocatalytic Strategies in Organic Synthesis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Photochemistry".

Deadline for manuscript submissions: closed (31 December 2019) | Viewed by 25597

Special Issue Editor

Dr. Davide Ravelli

E-Mail Website
Guest Editor
PhotoGreen Lab, Department of Chemistry, University of Pavia Viale Taramelli 12, 27100 Pavia, Italy
Interests: photocatalysis; green chemistry; radicals; organic synthesis; flow chemistry

Special Issue Information

Dear Colleagues,

It is difficult to exaggerate the importance that photocatalytic strategies have earned in recent years. Thanks to the unconventional pathways offered, they enable the smooth activation of substrates that would otherwise require harsh conditions to react, giving, at the same time, the desired products in excellent yields. Accordingly, photocatalytic processes are often considered as a superior choice when looking for an intrinsically green approach in the frame of organic synthesis. Indeed, recent trends involve the use of coloured catalysts, able to promote the desired processes under visible light irradiation or natural sunlight, further demonstrating the green potential of photocatalysis.

The seminal works by the groups of MacMillan, Yoon and Stephenson were published almost ten years ago now, igniting what can be considered an impressive “gold rush” of photocatalysis. This Special Issue wants to resume how far we have gone in this period and which future directions photocatalysis practitioners will move in.

Dr. Davide Ravelli
Guest Editor

Manuscript Submission Information

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Keywords

  • Photocatalysis
  • Photoredox catalysis
  • Photoinduced electron transfer
  • Hydrogen atom transfer
  • Organic synthesis
  • Green synthesis
  • Visible light
  • Solar light

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Published Papers (5 papers)

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Research

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8 pages, 1038 KiB  
Communication
Visible-light Promoted Atom Transfer Radical Addition−Elimination (ATRE) Reaction for the Synthesis of Fluoroalkylated Alkenes Using DMA as Electron-donor
by Wen-Wen Xu, Le Wang, Ting Mao, Jiwei Gu, Xiao-Fei Li and Chun-Yang He
Molecules 2020, 25(3), 508; https://doi.org/10.3390/molecules25030508 - 24 Jan 2020
Cited by 11 | Viewed by 3917
Abstract
Here, we describe a mild, catalyst-free and operationally-simple strategy for the direct fluoroalkylation of olefins driven by the photochemical activity of an electron donor−acceptor (EDA) complex between DMA and fluoroalkyl iodides. The significant advantages of this photochemical transformation are high efficiency, excellent functional [...] Read more.
Here, we describe a mild, catalyst-free and operationally-simple strategy for the direct fluoroalkylation of olefins driven by the photochemical activity of an electron donor−acceptor (EDA) complex between DMA and fluoroalkyl iodides. The significant advantages of this photochemical transformation are high efficiency, excellent functional group tolerance, and synthetic simplicity, thus providing a facile route for further application in pharmaceuticals and life sciences. Full article
(This article belongs to the Special Issue Photocatalytic Strategies in Organic Synthesis)
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Scheme 1

9 pages, 8482 KiB  
Communication
Precursor-Dependent Photocatalytic Activity of Carbon Dots
by Amadio Emanuele, Simone Cailotto, Carlotta Campalani, Lorenzo Branzi, Carlotta Raviola, Davide Ravelli, Elti Cattaruzza, Enrico Trave, Alvise Benedetti, Maurizio Selva and Alvise Perosa
Molecules 2020, 25(1), 101; https://doi.org/10.3390/molecules25010101 - 26 Dec 2019
Cited by 24 | Viewed by 4910
Abstract
This work systematically compares both structural features and photocatalytic performance of a series of graphitic and amorphous carbon dots (CDs) prepared in a bottom-up manner from fructose, glucose, and citric acid. We demonstrate that the carbon source and synthetic procedures diversely affect the [...] Read more.
This work systematically compares both structural features and photocatalytic performance of a series of graphitic and amorphous carbon dots (CDs) prepared in a bottom-up manner from fructose, glucose, and citric acid. We demonstrate that the carbon source and synthetic procedures diversely affect the structural and optical properties of the CDs, which in turn unpredictably influence their photo electron transfer ability. The latter was evaluated by studying the photo-reduction of methyl viologen. Overall, citric acid-CDs were found to provide the best photocatalytic performance followed by fructose- and glucose-CDs. However, while the graphitization of glucose- and citric acid-CDs favored the photo-reaction, a reverse structure–activity dependence was observed for fructose-CDs due to the formation of a large graphitic-like supramolecular assembly. This study highlights the complexity to design in advance photo-active bio-based carbon nanomaterials. Full article
(This article belongs to the Special Issue Photocatalytic Strategies in Organic Synthesis)
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10 pages, 3172 KiB  
Article
Photocatalytic Atom Transfer Radical Addition to Olefins Utilizing Novel Photocatalysts
by Errika Voutyritsa, Ierasia Triandafillidi, Nikolaos V. Tzouras, Nikolaos F. Nikitas, Eleftherios K. Pefkianakis, Georgios C. Vougioukalakis and Christoforos G. Kokotos
Molecules 2019, 24(9), 1644; https://doi.org/10.3390/molecules24091644 - 26 Apr 2019
Cited by 30 | Viewed by 6061
Abstract
Photocatalysis is a rapidly evolving area of research in modern organic synthesis. Among the traditional photocatalysts, metal-complexes based on ruthenium or iridium are the most common. Herein, we present the synthesis of two photoactive, ruthenium-based complexes bearing pyridine-quinoline or terpyridine ligands with extended [...] Read more.
Photocatalysis is a rapidly evolving area of research in modern organic synthesis. Among the traditional photocatalysts, metal-complexes based on ruthenium or iridium are the most common. Herein, we present the synthesis of two photoactive, ruthenium-based complexes bearing pyridine-quinoline or terpyridine ligands with extended aromatic conjugation. Our complexes were utilized in the atom transfer radical addition (ATRA) of haloalkanes to olefins, using bromoacetonitrile or bromotrichloromethane as the source of the alkyl group. The tailor-made ruthenium-based catalyst bearing the pyridine-quinoline bidentate ligand proved to be the best-performing photocatalyst, among a range of metal complexes and organocatalysts, efficiently catalyzing both reactions. These photocatalytic atom transfer protocols can be expanded into a broad scope of olefins. In both protocols, the photocatalytic reactions led to products in good to excellent isolated yields. Full article
(This article belongs to the Special Issue Photocatalytic Strategies in Organic Synthesis)
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8 pages, 895 KiB  
Article
Acid Catalyzed Formation of C–C and C–S Bonds via Excited State Proton Transfer
by Alessandro Strada, Mattia Fredditori, Giuseppe Zanoni and Stefano Protti
Molecules 2019, 24(7), 1318; https://doi.org/10.3390/molecules24071318 - 3 Apr 2019
Cited by 13 | Viewed by 3659
Abstract
The behavior of 2-naphthol and 7-bromo-2-naphthol as organic photoacids are exploited in organic synthesis for the preparation of benzyl sulfides (using a trichloroacetimidate derivative as the starting substrate) and polycyclic amines via acid catalyzed condensation of 1,2,3,4-tetrahydroisoquinoline with aldehydes. Full article
(This article belongs to the Special Issue Photocatalytic Strategies in Organic Synthesis)
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Review

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36 pages, 9775 KiB  
Review
Photocatalytic Difluoromethylation Reactions of Aromatic Compounds and Aliphatic Multiple C–C Bonds
by Sebastián Barata-Vallejo and Al Postigo
Molecules 2019, 24(24), 4483; https://doi.org/10.3390/molecules24244483 - 6 Dec 2019
Cited by 22 | Viewed by 6290
Abstract
Among the realm of visible light photocatalytic transformations, late-stage difluoromethylation reactions (introduction of difluoromethyl groups in the last stages of synthetic protocols) have played relevant roles as the CF2X group substitutions exert positive impacts on the physical properties of organic compounds [...] Read more.
Among the realm of visible light photocatalytic transformations, late-stage difluoromethylation reactions (introduction of difluoromethyl groups in the last stages of synthetic protocols) have played relevant roles as the CF2X group substitutions exert positive impacts on the physical properties of organic compounds including solubility, metabolic stability, and lipophilicity, which are tenets of considerable importance in pharmaceutical, agrochemical, and materials science. Visible-light-photocatalyzed difluoromethylation reactions are shown to be accomplished on (hetero)aromatic and carbon–carbon unsaturated aliphatic substrates under mild and environmentally benign conditions. Full article
(This article belongs to the Special Issue Photocatalytic Strategies in Organic Synthesis)
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